
House holiday rentals in Middletown
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Top-rated house rentals in Middletown
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Unique Dutch Barn in the Hudson Valley
The Unique Dutch Barn, is a magnificent property built in the 1800s and well located in the Hudson Valley on historic Westinghouse Farm. The perfect spot if you are here for a wedding, to visit West Point or LEGOLAND, go hiking, skiing or just to sample the local craft breweries and wineries. For art and music lovers Storm King, Dia Beacon and Bethel Woods are near. Whether you come for a creative retreat, or meet up with old friends and family, this expansive space will offer a memorable stay.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Fully stocked creekside sauna retreat with privacy
Welcome to Bluskyz! (Blue Skies) Perfectly nestled between the charming village of New Paltz and the beauty of the Gunks and it’s surrounding countryside. Quiet culdesac road close to everything, ONE HOUR FROM THREE MOUNTAINS and within walking distance to a couple of real country gems. Top of a hill, this home has amazing privacy, and the quiet of being the last home on a dead end street. With a natural spring pool, pergoladining, sauna in the back yard, your private spa in the Gunks awaits

Aster Place
A beautiful and cozy home nestled in the Forest Hills section of Greenwood Lake, just over an hour outside of New York City. Boasting nearby activities in each season, including wineries, skiing and lake activities, this is a perfect year-round retreat. located 1/2 mile from our quiet community beach allows for a serene daily chill by the water. Town center is a short drive away, or 15 minutes from all that Warwick has to offer, you will enjoy this perfect setting for your lakeside getaway!

TheGoshenGetawayPoolHotTubLegoLandArcade
TheGG is a beautiful spacious home with more amenities than one can ask for! Cooking for 10? We have options! Our double oven is perfect for holiday dinners! Not to mention our customs built outdoor kitchen and grill! Keep your kids entertained by throwing a pizza party using our beautiful stainless pizza oven! Burn those calories off in a private gym or laps in the heated pool MAY1ST Then relax in our 8per hot tub! Bring your clubs! Near by are four 18hole golf course with in a 15min drive!

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Peace and quiet. Comfy, private house to relax in
Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

Spectacular Lake Views from Every Room & Garden
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Cozy Rustic Farmhouse With Wood Stove
Make yourself at home in this unique farmhouse just an hour and a half away from NYC! Located right on the Bashakill Wildlife Refuge. this is the perfect getaway near Neversink Unique Area, Minnewaska State Park, Sam's Point, Legoland, and more! Enjoy the flicker of a wood-burning stove, make a BBQ feast on the outdoor deck, or admire the stars on a clear, dark night while sitting around the campfire. Good for couples, friends, or families–just no pets, please!

Modern creekside cabin in the Catskills
Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Luxury Mountain Retreat Condo - Skiing & More!
Newly renovated upper level 2 bedroom 2 full bath condo located in Great Gorge Village in Vernon, NJ. Enjoy the beautiful views and create memories in our cozy condo. In close proximity to Mountain Creek resort where there is skiing, snowboarding, waterparks/rides, and mountain biking. Close to Crystal Spring as well with award winning golf courses. Up the road from Minerals Resort.

Eagle Rock House
FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Eagle Rock House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space.
Popular amenities for Middletown house rentals
House rentals with a pool

midcentury mod * HOT TUB * walk out trail 2 mohonk

Private Retreat w/Pool, Hot Tub & Fire Pit, 6 BR

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

Private Dock/Indoor Pool/Sauna/Hot Tub - Sleeps 14

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Family Fun w Hot tub/Pool/Sauna near Ski Holidaymt
Weekly house rentals

Fairway Retreat - Montgomery, NY

Private Large Villa With Pool

Serene Hudson Valley Escape Hottub/Pool/King Suite

Cozy Greenville Getaway

Lake house, ONE HOUR from NYC

Mt. Wonder: Cozy Cabin w/ Hot Tub and Wow View

Lakefront Oasis with a Private Beach

5Bdrm Estate/Tennis near LegoLand
Private house rentals

The Wooden Igloo Near Legoland NY

Welcome to Newburgh's Cozy Cove

Starlight House - Swinging Bridge Lake

The Alexandria - Wurstboro, NY

Mohonk Abode | dog friendly + near hiking

Cabin with a View

The Montgomery Chalet

Lovely Private Home w/Mountain Views and Pond
Quick stats about house rentals in Middletown

Total holiday rentals
Explore 10 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 50 verified reviews to help you choose

Wi-Fi availability
10 of Middletown holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Middletown rentals

4.7 Average rating
Middletown stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- MetLife Stadium
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Yankee Stadium
- Bethel Woods Center for the Arts
- Bushkill Falls
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Resorts World Catskills
- Delaware Water Gap National Recreation Area
- New York Botanical Garden
- Shawnee Mountain Ski Area
- Mount Peter Ski Area
- American Dream
- Brotherhood, America's Oldest Winery
- Riverside Park
- Promised Land State Park
- Bear Mountain State Park
- St. Nicholas Park
- Wawayanda State Park
- Opus 40
- Paterson Great Falls National Historical Park
- Nickelodeon Universe
- Claws 'N' Paws




